


It's Dare (Uhh)

by FrizzleFry



Category: Recess (Cartoon)
Genre: Anal Fingering, Anal Sex, Chubby Kink, Dildos, Embarrassing confessions, F/M, Femdom, Light dom/sub undertones, Overstimulation, Painful Sex, Pegging, Rough Sex, Truth or Dare, Underage Drinking, and not really dubcon, ass, bc he's super late, but some boundary pushing that could be read as such, but still mostly prepubescent TJ, do not try this at home, teenaged
Language: English
Status: Completed
Published: 2020-12-23
Updated: 2020-12-24
Packaged: 2021-03-10 16:48:06
Rating: Explicit
Warnings: Underage
Chapters: 3
Words: 7,757
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28250385
Author URL: https://archiveofourown.org/users/FrizzleFry/pseuds/FrizzleFry
Summary: It isn't every day that a night that started with illegal drinking ends with a strap on and a wire fence, but that sure as fuck happens in this.
Relationships: T. J. Detweiler/Ashley Spinelli
Comments: 4
Kudos: 12





	1. the part you're most likely gonna skip to get to the smut

**Author's Note:**

> After almost a whole year I wrote TJ again! Woooo!

“Shit!” she shouted, pointing the bottle in her hand straight down to see if any drops would come out.  
“What's wrong?” TJ asked. His cheeks looked rosy in the dim moonlight. His legs were dangling off the old table they were sitting on. He had taken off his jacket because it got too warm for him and was now sitting there in just his jeans and his shirt. Spinelli found that astounding, but she was used to wearing a leather jacket in even the hottest of summer.  
“Bottle's empty again,” Spinelli answered, pointing the opening straight at him.  
“What do you mean _again_ , did you refill it?”  
“You know what I mean, smart ass.”  
“Oh do I?” he teased her and she glared at him.  
“I will chuck this at your head.” She held up the bottle like a bat.  
TJ chuckled.  
  
“Guess that's it, huh?”  
“Aren't there any more?” she asked.  
“Nope.”  
“So what now?”  
“I don't know, I've never been this drunk, dunno what comes next.” He stretched his arms out in front of him.  
“You drank three beers.”  
“Yeah and that's-” He began counting with his fingers “One, two... three more than ever before.”  
“You're shitting me, right?” she looked at him with her eyes wide.  
“ _This_ was your first time drinking?”  
He nodded, smiling.  
“And I took you to some shitty playground for it just because I felt bored hanging out at home.”  
He nodded again.  
“I mean it's better than my first time I guess...”  
Neither said anything for a while.  
“Welcome to teenage life I guess? In a way there is no better way to start than illegal drinking at a fenced off elementary school playground.”  
“Oh what a warm welcome. I'd do it again.”  
“You're officially eligible to grow hair on your balls now, congrats. I know you need it.”  
He flipped the bird at her and laughed. It was no secret that he was... late. Late as in “he looked like an eleven year old”, kind of late. It was fairly obvious and Spinelli knew, if anyone but his closest friends teased him about it he would probably have been super pissed.  
  
“I dare you to do ten jumping jacks.” She put the bottle down on the table between them and pointed it at him.  
“What?” He looked at her, puzzled.  
“We're playing truth or dare.”  
“Why?”  
“Because I'm bored and you are, too, and it's fun and it's even more fun when you're drunk.”  
“Why don't I get a choice between truth or dare?” he asked.  
“What, do you wanna get out of doing sports?”  
“Yes. I don't feel like I don't even wanna do _one_ jumping jack, let alone ten.”  
“I warn you, you will regret every time you chose truth.”  
He thought for a moment.  
“Bring it on!”  
“Do you actually still have no hair on your balls?” She didn't even hesitate.  
“Going in straight for the kill are you?” he laughed. “No, I don't.”  
“Are you embarrassed about it?” she asked.  
“No, no, no, no, no, you had your truth, this is my turn.”  
“Ok, fine, but you gotta spin the bottle first.”  
“Spin the bottle? What for? We're two people.”  
“Just do it.”  
“Fiiiine....” he sighed and turned the bottle over to point at her.  
  
“So...” she began.  
“Dare.”  
“I dare.... _you_ to do ten jumping jacks.”  
“Pff... easy,” she said.  
She took off her jacket and proceeded to to as told. She didn't break a sweat, or struggle with her sense of balance for one second.  
“So you're really that sober are you?”  
“Nah, I'm just good at this.”  
She sat back down and turned the bottle at him.  
  
“Truth,” he said almost immediately.  
“Are you embarrassed about... you know... that whole thing?” she asked.  
“What do you think?” he asked back. “Yes. I mean... who wouldn't?”  
“I don't know, puberty kinda sucks. I'd like to go back to not having periods.”  
He was silent for a while.  
“I _am_ in puberty, it just doesn't register with my body very much.”  
He pointed the bottle at her, hopeful to change the subject.  
  
“Truth or dare?” he asked.  
“Dare.”  
“I dare you to choose truth,” he said.  
“That's cheating.”  
“So?”  
“Fiiiiiine,” she groaned. “Truth.”  
“Why was your first time drinking so bad?”  
She paused.  
“So...” she started. “There was this guy. And I wanted to impress him.”  
“What guy? Do I know him?”  
“Yeah, but this story's confidential, so I am not gonna tell you who.”  
TJ chuckled.  
“So anyway, we were hanging out with a bunch of his friends and they're drinking lemon drops but like... poorly.”  
“What's a lemon drop and how do you drink it poorly?” TJ asked.  
“It's vodka and you drink it poorly by overestimating yourself.”  
“Huh...” TJ nodded.  
“So anyway everyone's passed out, or gone home, there's vomit on the floor and I'd much rather be home as well, but I promised to stay.  
This guy is so gone and suddenly he starts bawling his eyes out. So I had to play nurse -slash- therapist for him for hours till he passed out.”  
“That sounds shitty.”  
“It was.”  
“Is he ok?”  
“Probably not but that's not my problem, he's an ass.”  
She pointed the bottle at him.  
  
“Truth,” he said.  
“Why are you so afraid of taking dares? The worst that can happen is falling on your ass.”  
“I...” he paused. “I don't like doing sports when people watch me. I suck at them and it makes me feel... you know...”  
“I genuinely actually don't.”  
“Do I have to say it?” he asked.  
“Say what?”  
“Like some bumbling, fat kid who sucks at sports and who people laugh at.”  
He looked away, flushed.  
“You always did sports though back when we still played kickball in recess.”  
“Well, back then everyone else wasn't some... puberty machine thing.”  
He pointed the bottle at her, seeming desperate to change the topic again.  
  
“Truth,” she said.  
“Have you and Lance fucked?”  
“Yeah, but we're not very compatible.”  
“What do you mean by that?”  
She pointed the bottle at him.  
  
“Truth or dare?”  
“Gonna leave me hanging like that?” he asked.  
“Yes,” she said. “Truth or dare?”  
“Truth.”  
“Tits, or ass?” she asked.  
“What?”  
“Tits, or ass? It's not a complicated question.”  
“Both? Neither? I don't know.”  
“Come on, you gotta have some preference.”  
“I honestly don't know, I don't really like... _that_.”  
“Are you gay or what?”  
TJ pointed the bottle at her.  
  
“Truth or dare?”  
“Truth.”  
“Why were you incompatible?” he asked.  
“Are you sure you wanna ask me that?”  
He nodded.  
“Are you _sure_ , really, really _sure_ , you wanna know?”  
“What, did you kill someone, or what?” he asked.  
“He wanted to be in control and he didn't like things that made him feel submissive.”  
“Like what?”  
“Like touching his ass in any shape, or calling him a good boy, or the fact that I am taller than him.”  
“What did you wanna touch his ass for?” he asked.  
“Are you kidding?” she shot back. “Asses are the best part of the human body.”  
“So did you wanna like-”  
“Truth or dare, Detweiler?” She pointed the bottle at him.  
  
“Truth.”  
“Are you gay?”  
“I...” He didn't know how to answer that.  
“Is that a yes?”  
“I have no idea....” he muttered, barely audible.  
“What, you gotta know what turns you on, right?”  
“Do I? Because I don't. I don't even know who I even really like.”  
He pointed the bottle at her.  
  
“Truth or dare.”  
“Fine, truth,” she sighed.  
“So... did you wanna like... do stuff with his ass?” he asked.  
“Yeah.”  
“Like what?”  
“Anything really, but he'd say that's gay.” She laughed.  
“Fucking rich, to complain about how gay having sex with a girl is. Men are super weird about that.”  
“Ok, but like... like what?” he asked.  
“You know...”  
“I don't.”  
“Fingering him, eating him out, pegging him.”  
“Pegging?”  
“Fucking him with a dildo.”  
“Oh...”  
“Anyway...” she said and pointed the bottle at him.  
  
“Truth,” he said.  
“Were you and Ashley A actually fucking, or did you just tell everyone that?”  
He paused.  
“ _We_ didn't even tell anyone that. We just decided it might be better to not correct people after the word spread around.”  
Spinelli laughed out loud.  
“To think I was actually jealous.”  
“You were jealous?” he asked.  
“Point the bottle if you wanna know.”  
He pointed the bottle at her.  
  
“You were actually jealous?”  
“Yeah I was.”  
“So... you were crushing on me?”  
“Not really, no, I was just territorial.”  
He paused.  
“Huh...”  
“Truth or Dare?” She pointed the bottle at him.  
  
“Truth.”  
“So how did you feel about her?”  
“She's nice, and all, but not like... she doesn't feel like she's really there on that level, not like...”  
“Not like who?” She grinned at him.  
He pointed the bottle at her.  
  
“Truth,” she said.  
“So are guys really into that stuff?”  
She laughed.  
“Guys who know what's good are. Most are too hung up about that whole gay thing.”  
“So-” TJ began, but was interrupted.  
“Times up, truth or dare?”  
She pointed the bottle at him.  
  
“Dare.” He gave her a cheeky grin.  
“You know what I am going to ask and trying to weasel yourself out of that.”  
“Maybe.”  
“If you choose dare now I will make you show me your hairless, little baby balls and you will sit your naked ass down here on this cold ass table, so I would be careful what you choose now.”  
“That's blackmail!”  
“Yes it is,” she smiled.  
“Fine... truth.”  
“So... like who?”  
“This is weird,” he said.  
“What is?” she asked.  
“Basically my friends.”  
There was a pause.  
“All of them?” she asked.  
“Close ones,” he said. “Like... Vince, Mikey, Gus, Gretch... you... Franklin too I guess.”  
She laughed.  
“You're crushing on Mr. Dude?”  
His face was as red as it would probably ever get.  
“I... I think?”  
“So... you're bi then?”  
“I don't know... I don't feel like guys are hot... or girls... I just feel like _you_ guys are hot.”  
She smirked.  
“So you find me hot?” she asked.  
“Are you kidding!?”  
She looked at him expectantly.  
“Yes, you're fire,” he blurted out.  
“Hey, TJ?”  
“Yeah?”  
She pointed the bottle at herself.  
  
“For my next truth I want you to ask me who at our school has the hottest ass.”  
“Ok?”  
“Ask me.”  
“Who at our school has the hottest ass?”  
“You.” She points at him.  
“You're predictable,” he said.  
“You're a hot piece of ass,” she shot back.  
  
“So this is awkward,” he said after a while.  
“How so?” she asked.  
“Us both kinda confessing like that.”  
“It's only awkward if you make it so.”  
“Wait... you said you weren't into me!”  
“I lied.”  
“You can't lie in truth or dare!”  
“I did. But not even really, it's complicated. I only really realized I was into you after that, so I technically said the truth.”  
“Saved by a technicality...” he shook his head.  
She pointed the bottle at him.  
  
“Truth,” he said.  
“How are you feeling now?”  
“Not too bad I guess... I kinda feel free...”  
He pointed the bottle at her.  
  
“Truth,” she said.  
“How does it feel to do butt stuff?” he asked.  
“For me, or for the guy?” she asked back.  
“Both?”  
“Well for me it feels really nice. Even if I am not really getting any penetration of stimulation during it unless I do it myself... I like seeing guys squirm in front of me and I like to break through that stupid macho facade and let them experience that kind of... letting themselves fall down into pleasure.  
For the guys I can't really tell specifically, I am not one.  
Say, have you ever fingered yourself?”  
She pointed the bottle at him.  
  
He shook his head.  
“I don't even know... how? If that makes sense for something so obvious?”  
He pointed the bottle at her.  
  
“Have you ever thought about... doing that to me?”  
She laughed.  
“What a waste of a question. Obviously yes, I think about it a lot.”  
“Oh...” He gave an awkward laugh as well.  
She pointed the bottle at him and looked him in the eyes.  
  
“Truth or dare?”  
He gulped.  
“Truth?”  
“Are you going to choose dare if I ask you to?”  
“I... I might?”  
She paused and then took the bottle away.  
  
“I truth you to dare.”  
“That doesn't make any sense,” he laughed.  
“ _You_ don't make any sense!”  
“No, you!”  
“Look, it sounded better in my head, okay?”  
“Okay, okay... dare.”  
“Drop your pants and show me what you've got.”


	2. the part you don't skip outright but skim through till the *really* juicy bits start happening

**Notes for the Chapter:**

> Probably gonna finish this on Christmas Eve, so that's kinda neat.

He was hastily fumbling with his belt and with a clanking noise it opened.  
Spinelli giggled when she saw his Señor Fusion boxers.  
“What are you laughing about?” he asked.  
“You're just cute” she said, making him blush.  
He turned away from her as he pulled down his pants, exposing his butt first to her. Even in the dim light it was visibly full of freckles and she couldn't keep herself from immediately staring. Two perfectly smooth, chubby cheeks that no doubt hid a beautiful little butt hole.  
“Damn,” she mouthed under her breath.  
He turned around, cupping his privates in his hands and blushing hard.  
“Come on, lemme see.”  
“A... are...” he stuttered. “Are you sure?”  
She nodded and he took his hand away.  
He was completely hairless, his dick hung flaccid and small beneath a mound of pubic fat that it was sinking into just ever so slightly at the base and resting on his equally small balls.  
“Damn, you weren't lying.”  
“Not very impressive, is it?”  
“It's not very big, but definitely impressive,” she said.  
He just looked at her, puzzled.  
“You're beautiful... just like I imagined, but better.”  
“You're just lying to make me feel better.” he said.  
“No I ain't, you're gorgeous.” She put on a seductive tone of voice. “I wanna kiss and bite every one of the freckles on your ass.”  
He covered his face with his hands, mouthing an “Oh my god.”

“Come, sit back down,” she said.  
He slowly waddled back to the table with the pants around his ankles inhibiting his movement before getting annoyed, kicking off his shoes and pants with them and sitting back down next to Spinelli.  
He shivered from the cold against his butt.  
“So...” he said.  
“So...” she said.  
After a while of silence it was her who spoke again first.  
“I can't believe your ass. I didn't think you'd have freckles there, too.”  
“I have freckles in a lot of places,” he said.  
“Like?”  
“The insides of my thighs, my belly, my collarbone...”  
He pulled up his shirt, showing the freckled rolls of fat on his belly.  
“Damn, you're so pretty.”  
“So... truth or dare,” he asked.  
He couldn't find the bottle anymore.  
“Dare.”  
“I dare you to do all of these things with me you wanna do.”  
“Are... are you sure?” she asked.  
He nodded.  
“Are you  _really_ sure? You're drunk, you know, and I am too.”  
He nodded again.  
“I wanna know what it's like and you already saw my dick so I don't see why not to do more.”  
“You're a virgin, and this is how you wanna get your cherry popped?”  
He nodded for a third time.  
“Yes, it is, I couldn't imagine a better way.”

“Okay,” she said. “Lay down on your back and spread your legs apart a little.”  
He did as told and she moved one hand below his shirt to rub his belly. It felt so soft and pliable between her fingers. His still soft dick twitched nervously and she had to stifle a giggle.  
With her other hand she gently cupped his balls, rubbing her thumb over the smooth skin.  
He sucked in a breath. Goosebumps spread through his entire body.  
“Sensitive, are you?” she asked to no answer and began rolling the small testicles between her fingers, putting on just a little bit of pressure to see his response, which happened in the form of his dick twitching up to a half mast.  
She put on a little more pressure and he let out a moan.  
“So that's how you swing,” she chuckled.  
She wandered a little lower, still not touching his dick and instead massaging his taint. He merely kept twitching and growing harder before her. She looked at his face to find him looking longingly at her. Oh god, that look could kill someone with the sheer adoration.  
He was fully hardt by now and she moved down with the hand on his belly to draw light circles around the tip of his foreskin, finding him just ever so slightly slippery.  
She slowly pulled down, unveiling his head, purple and swollen, but looking so cute on his perfectly smooth dick.  
“You look so young, god damn,” she said while moving her hand down to his base, still just teasing his length, giving it the softest touch she could that he'd still feel while moving her other hand a little bit lower to edge of the small part of his butt crack that was available to her in that position.  
“Doesn't that weird you out?” he asked in between soft moans. “That I'm like... a kid?”  
She paused for a second.  
“Don't take this the wrong way, but... I'm kinda into it.”  
“Oh....”

“I didn't make it weird just now, did I?”  
He shook his head.  
“Not any weirder than it already was.”  
“Ok.” She nodded. “Pull up your legs so we can get to the good stuff.”  
He pulled up his legs and put his hands behind the backs of his knees.  
“Like this?”  
“Perfect.”  
He was completely exposed now, his cheeks pulled apart by the position he was in, and his little pucker looked absolutely perfect to Spinelli. Thanks to the full moon she could actually see it at all and there couldn't have been a more perfect hole to sit on his perfect ass. Combined with the way his shirt was riding up on his belly, just barely exposing the underside of his tummy and his needy erection it made Spinelli bite her teeth with the need to wreck him.  
“This is so embarrassing,” he said.  
“You're beautiful though.”  
“Am I? How beautiful could some fat kid's asshole be?”  
She laughed.  
“Oh you'd be surprised.”  
She lubed her finger with spit and moved it close to his hole.  
“Ready?” she asked.  
He nodded and she touched the tip against him.  
Holy fuck, he was warm. She felt like she was touching a radiator.  
He let out a nervous chuckle that turned into a squeak when she started to draw circles around his entrance.  
“You really haven't ever done this before, l-m-a-o,” she laughed.  
“Nope, but it feels really weird.  
Also embarrassing.  
Please don't stop though.”

She kept going until she noticed her finger was going dry, pulling all kinds of moans and squeaks and relaxed sighs from the boy in front of her.  
When she put her finger back in her mouth to re-lube it he looked at her, questioning.  
“Isn't that gross?” he asked.  
She didn't answer. Instead she moved behind him and in one huge slurp she licked all the way from his tailbone up to his balls. His eyes shot open and he breathed in sharply.  
“No, it isn't,” she said finally. “You could stand to shower a little more thoroughly, but I kinda like it.”  
She didn't even have to look at his face to know how tomato red he must have been now.  
Again she wet her finger and this time she pushed with a little bit of force. Not enough to enter him yet, but enough to make him notice and gasp.  
“So now you push out to make it easier for both of us,” she said.  
“Like this?” He pushed against her and the tip of her finger slipped inside just a little bit, not yet inside of him, but surrounded by the ring of his hole.  
“Like that,” she said. “How does it feel so far?”  
He was still rock hard, so she wasn't surprised when he just moaned out.  
“It's like... I don't even know, how deep are you in me already?”  
Spinelli laughed.  
“Like half an inch?”  
“Oh...” he said. “Fuck.”

She slowly pushed into him and reveled in how soft and warm and tight he was. It'd be so much fun to just go full on on him, but she took her time letting him get used to having something inside him.  
“How's it now?” she asked.  
“People take whole dicks up there?” he asked. “That's crazy.”  
“You're so cute, I wanna ruin you,” she said.  
“That's kinda hot,” he said.  
“Oh?” She looked him in the eyes. “You like the thought of getting wrecked?”  
“I mean, kinda? It's kinda exciting to be in danger.”  
She began moving her finger inside of him, pushing against the soft, velvety walls of his rectum. He squeezed his eyes shut and held his breath while shifting around on the table as much as he could without leaving his position.  
“Dude, you're so cute like that,” she chuckled.  
She put her finger against his prostate and pressed down. He let out a high pitched moan.  
“Like it?”  
He nodded.  
“I can't hear you,” she said.  
“Yes,” he groaned.  
“Yes  _what_ ?”  
“It feels good.”

She pulled out and re-lubed her finger, adding a second one this time, then moved back to his butt.  
She slipped in with her middle finger first, pulling a gasp from TJ, then put the tip of the second up to his hole.  
“Ready?”  
He nodded.  
Then he grunted when she pushed in the second finger.  
“Hows's that now?” she asked.  
He didn't answer, just clenched his teeth.  
She went back to massaging his prostate and he relaxed a little bit.  
“You're doing so good, baby.” She pet his hair with her hand. He closed his eyes and leaned into her hand.  
She moved her fingers against each other inside of him, drinking up the feeling of warmth and tenderness, reveling in the power she had over him, how he was like butter between her hands, ready to melt at her command. Listening to all the mewls and other noises he made, the breathy sighs, the high pitched moans, the strained grunts, feeling how gradually he grew softer around her as his hole got used to the stretch.  
She started to pull her fingers apart ever so slightly to push his limits a little more, carefully watching his face react to all those new feelings he couldn't even have imagined just minutes ago.

After a while she added her ring finger, first arranging the three intruding appendages in a triangle to make the circumference minimal and the intrusion most painless and then very gradually flaring out to pull him open.  
He took it like a champ, still rock hard all the way through, shifting and arching his back beneath her, but never pulling away, or clenching down. He wanted this. He loved it. She could feel his body long for more, even if he was on the barrier of pain overcoming pleasure whenever she started to spread apart her fingers.  
Deciding to be a little bit evil and have some fun with him, she pushed her fingers apart noticeably wider than before. He all but yelled out in some noise that quickly turned into a squeak and then a silent cry.  
“There, there, you're doing so good.” She caressed his cheek and looked him in the eyes. He looked back at her with adoration and a small tear gathering at the side of his eye.  
“I love how well you're taking it and how you still push against me. You're doing amazing.”  
His dick noticeably bounced upward at hearing that. He was clenching down a little bit on her fingers while his dick thrust into the air repeatedly.  
“Someone want some attention?” Spinelli asked and chuckled.  
“Ahhhh...” His voice was hoarse and whispery.

She moved all her fingers to push against his prostate and moved her other hand to his dick, pumping him slowly.  
He screwed his eyes shut and arched his back, thrusting into her hand. Pre come was dripping from his tip.  
Almost immediately she could feel his prostate seize up and grow much firmer. He was gonna come any second now. He clenched around her fingers hard and she increased the grip strength around his dick, as well as the tempo. And then it happened. His load wasn't huge exactly, but definitely larger than she expected. And powerful. The first shot flew right over his head with little bits just barely landing on his face. The second and third landed on his shirt and the exposed part of his belly.  
She let him ride out his orgasm for a couple seconds until the clenching stopped, still knuckle deep inside of him and playing with his dick, that was quickly growing flaccid now. He was so sensitive. Any slight touch to his head made him squeak out and moan and pull away, to no avail.  
Spinelli chuckled, she could spend ages overstimulating the boy, but decided it might be better not to push it  _too_ much on his first time.  
She slowly pulled out of him, pulling a heavy sigh from him in return, admiring his now shiny and slightly swollen hole before laying down next to him.  
He finally let his legs down and lay there, silent, or... rather without a word, because his breathing was heavy and labored and it echoed through the whole playground.  
She put her hand, still wet with her spit and feeling warm from the inside of his butt hole on his belly, rubbing the cum drops into the fabric and getting it sticky and slimy. She could feel his heartbeat, strong and fast, through his entire belly, as it heaved and sank beneath her palm.

“How was that?”  
TJ had finally caught his breath... somewhat.  
“How do you think it was?”  
“Can you believe how many guys just never even wanna hear of it bc they think it will turn them into a girl?” she asked.  
TJ looked at her skeptically.  
“They don't really believe that,” he said.  
Spinelli sighed.  
“They don't say it out loud because they realize how dumb it would make them sound but really they believe it deep down where their fears don't make sense.”  
“That's wild. I feel more like a boy than ever.” He chuckled.  
“You're good as a boy. More guys should be like you.”  
“You mean small and without pubes?”  
“Yes, but also less afraid of enjoying life.”  
  
“When you were inside of me I could feel all of your movements. I didn't even know I had nerves down there,” he said.  
“You'd be surprised how many things you don't really know you can actually feel till you do.”  
“When you hit that spot... it felt like my entire lower body was like... it was my dick and I was grinding against my mattress.”  
“Is that something you do?” Spinelli laughed.  
TJ blushed.  
“Yeah...”  
“You're so adorable.” She gave him a small peck on the cheek.  
“You know... it's like...” he began. “Like when you do exercise and parts of your hurt afterwards that you didn't even know you had. But the opposite, but also played straight, jesus, I feel sore.”  
They both laughed.  
He began speaking again.  
“Too bad that we couldn't do that other thing?”  
“What thing?” she asked.  
“That thing with the dildo where you fuck someone.”  
“Oh, you mean pegging... well...”  
She looked away, blushing.  
“Well what?” he asked.  
“Well...”


	3. the part that you actually came for but you should probaby read the other chapters anyway

**Notes for the Chapter:**

> See it as a christmas gift.

“I mean... we could,” she looked away from his face.  
“Do you mean you...”  
“If you laugh at me I will come and murder you in your sleep, understood?”  
“Why would I laugh at you?” he asked.  
She opened her zipper and pulled down her pants to reveal a harness that was strung over her underwear.  
He looked at her puzzled.  
“I am not laughing, but why are you wearing that?”  
She flushed.  
“It's a comfort thing. Makes me feel strong.”  
He chuckled.  
“That's kinda cool.”

She began rummaging through her backpack, pulling out a small bottle and a black satchel and laying them down next to TJ.  
“Are those comfort things, too?” he asked.  
“I kiiiinda was gonna go on a date tonight,” Spinelli said.  
“What do you mean _kinda_ ? Am I a rebound?”  
“No, I cancelled it bc I wasn't feeling up to it and then you called. And I just... didn't change my backpack.”  
“Why'd you tell me about the harness if you brought it anyway bc of that?”  
She looked at him like he just asked the most obvious thing ever.  
“You don't lie during truth or dare. Not even by omission.”  
“Huh...”  
She put her hand into the satchel and pulled out a rather sizable, deep black dildo. It wasn't tooooo long (though definitely a great deal longer than TJ was) but was pretty thick and grew thicker around the middle.  
“I should tell you,” she began. “This is not a beginner toy, it's gonna take some effort and likely come with some pain at first.”  
He gulped.  
“You still wanna do it?” she asked.  
He nodded.  
“Yeah... it's... I'll live,” he said.  
“Okay.” She began securing it in her harness.  
“How do we do this?” he asked.  
She thought for a moment.  
“Do you wanna be in control, or do you wanna take it?” she asked.  
“Take it, I guess?”  
“That's what I hoped for.” A grin spread across her face. “How stable do you think this table is?”  
“It held up so far,” he said.  
“Okay.”

She directed him to kneel down on all fours with his face down, resting on his jacket and his butt in the air. Spinelli behind him admired the view. The freckled cheeks, soft, round, fat, parted to reveal a beautiful, already slightly puffy and bruised hole. His thighs looking tender enough to just take a bite out of. His balls hanging between them, small and smooth, begging to be played with, or possibly to be played with extra roughly, but that should be for another day.  
“Push out again,” she commanded while she slathered the dildo with lube.  
Immediately she could see him pucker up, inviting her in.  
She put the tip against him and he shivered. So sensitive. He was probably more sore than he let on, considering it was his first time ever to have anything up there.  
She started to push, watching the tip force it's way inside of him, pulling him open.  
He let out a strained grunt that turned into a whimper soon when the dildo began widening. She stood still, letting him adjust. He still wasn't pulling away. Such a brave little trooper.  
His breathing was fast and shaky. His hands grabbing onto the splintered edges of the table and gripping down hard.  
She stroked his back with one hand, and kept the other steady on his butt.  
“You're doing so good, just get used to it, It'll get much better soon.”

She put a little more pressure on it, pulling a loud gasp from him. Very slowly she inched forward, nearing the thickest part.  
“You're almost at the biggest part, then it'll get easier again.”  
Watching him be stretched apart like that was hypnotic. She wanted so bad to let herself go and just wreck him completely without abandon. But she couldn't. Not yet.  
His breathing grew more irregular and he started letting out a sob here and there when she reached the thickest part. What wouldn't she have given to see his face right now.  
Then, as the thickest part stretched him open as far as he would go, she slipped in completely in one swift motion.  
The shriek he gave was one of both relief and another type of pain. Or maybe less pain and more something incredibly intense he had no idea was possible for him to experience.  
“You ok, baby?” she asked.  
He let out a near intelligible sound that Spinelli figured was closer to a yes than to a no.  
“I'll let you get used to it for a bit. Getting filled up so much can be overwhelming if you're new to it.”  
After a while he seemed to have gathered enough of his wits to speak again.  
“It hurt, but... I would do it again. Is that weird?”  
“Oh baby,” she began. “Nothing weird about that. You love it rough, don't you?”  
“Yeah... I guess...”

They were both silent for a moment. Spinelli was listening to his breathing calming down gradually.  
“When it slipped in completely,” he began. “It was like I was suddenly being stabbed. But It didn't hurt, it just... it felt like it was entering my tummy from the inside and I could feel all my organs move... that probably sounds dumb...”  
“Nah, that sounds about right... your butt is sensitive, things just feel like that.”  
“It feels nice to be so... full...”  
“Yeah?” she asked.  
“Yeah,” he answered.  
Deciding he has had enough time to get used to it she pulled out completely.  
He gave out a little shriek again as he was stretched open so quickly.  
“Spinelli...” he moaned.  
“Yes?”  
“Please... I feel empty.”

She lined herself up with his hole again and started pushing. He clenched his hands again as it ripped him open, but he didn't start sobbing again.  
“Ahh...”  
“You like that?” she asked.  
“Yes.”  
She pulled out and stopped right at the thickest part.  
“You like this too?”  
“Ugh... yes,” he grunted.  
“You want me to fucking ruin you?”  
“Ye.... yes, ma'am.”  
Spinelli did a double take and so did TJ judging by the way his body suddenly went stiff.  
“Did you just...?”  
“Yeah...” he said, barely audible and buried his face even deeper in his jacket.  
“Fuck yeah!” Spinelli shouted out and slapped TJ's ass.  
He winced.  
“How about that?” she asked.  
“Yes!” he shouted, muffled.  
She dove in again with much more force than before and he choked on a gasp. Before he could say anything she pulled out till just the tip was inside and dove back in until she bottomed out.  
“God you're so beautiful like that,” she said.

Seeing the dildo, herself, disappear into him, stretch him apart and imagining how it was filling him out, intruding into his deepest parts, the wet and squelching sounds they made, she savoured every moment. Every shiver, every twitch, every sound he made. Every gasp, moan, squeak, sigh and choked up yell, muffled from the jacket still. His hands were still grabbing onto the edge of the table, holding on for dear life.  
As she got into a rhythm he cycled back and forth between being tense, bracing himself for her, steadying himself and letting lose, relaxing, letting himself be shaken like he was made of jelly. With every thrust ripples spread from his butt down his thighs and up towards his back.  
At some point he started moving against her, seeking the rough and deep fucking and wanting more friction, harder punches into his guts, faster thrusts.  
Spinelli marveled at how much he was visibly enjoying it. When she slipped out at one point and could briefly see below him without any trouble she saw that he was leaking pre-come onto the table. He was completely limp and focused on his ass, but still she was driving the pre out of him with every thrust.  
She put the tip in again and remained still.  
“Work for it,” she said. “Move a little.”

And so he did. He moved himself back and forth as fast as he could, his jiggling ass smacking against her hips every time with quite some force like he was trying to go deeper, further, harder than was possible. That he still had that kind of strength inside him at all was amazing, but it also made her dedicated to tiring him out completely. Make his entire body so sore that he couldn't move at all on the next morning.  
He had to support himself on his hands now to push against her more easily so the string of moans and grunts and other noises coming from his lips weren't muffled anymore. He sounded like an angel if angels ever get their guts blown out with a very non beginner friendly strap on that is.  
At one point his moaning got significantly more intense and he started pressing himself as tightly against her as he could. His hole was clenching around her and his entire body went stiff. He grabbed his belly with one hand. The clenching must have been really uncomfortable with him being filled out so much, but that probably just added to his orgasm.  
After a while he sank down and off the dildo, looking almost passed out. Then he turned around, wincing when he realized that his body hurt with every movement and lied down on his back.

His knees were raw and even bloody in spots, his palms were similarly pink. His face was streaked with dried tears and his eyes were still red. His lower lip had dried blood on it. He probably bit down on it too hard at one point, or scraped it against his jacket's zipper while getting rubbed over the table.  
“That was amazing,” he breathed out. His belly was rising and falling rapidly as he tried to get some oxygen into his lungs. “Fucking, amazing.”  
Spinelli smirked. Looking at the fence that caged off the playground gave her a deliciously evil idea.  
“Who said we're done?” she smiled at him.  
“What?” He looked at her puzzled. “I don't think I can still move like that.”  
“Oh that won't be a problem. You're not wimping out just when things go the most heated, are you?”  
She could see the arousal on his face. He was considering wether doing all of that again would be even better than the last time, or if it would just kill him. Or maybe both.  
“What do you have in mind?” he asked.  
She jumped off the table and pulled him upright, then to the edge, and then took him into her arms. She pulled him off and was now carrying him with one hand on his back, one on his ass, with his legs slung around her hips and his arms around her neck.  
He was heavy, but less so than she expected. All that lifting was finally gonna pay off. Hes body resting so completely in her arms felt so warm and soft.  
She walked him over to the fence and pushed his back against it, kinda worried about pushing it over, since it looked a little flimsy, but it seemed to support them just fine.

“Should I...” TJ began.  
“Just hold onto the fence, can you do that, baby?”  
Being asked like that seemed to reinvigorate him. He pulled up both his arms and locked his fingers into the mesh of the fence above his head. His legs were still wrapped around her hips. She removed the hand on his butt to line herself up with him. The tip pressed against his entrance and he winced.  
“Ready, baby?”  
He nodded.  
She pushed upward and saw his face go through all the emotions a person could feel in a split second. Just inches from hers, she could finally admire how beautiful he was like that. His hair sticky with sweat, his eyes closed in this mixture of pleasure and exhaustive pain. His cheeks flushed red. She pressed a kiss onto his lips, tasting the dried blood on him and started to move.

She couldn't move as quickly and harshly as before but she didn't need to. Gravity was doing it's job to drive her deep inside of him. She lowered and raised her hips, as well as pulling him up and letting him fall down onto her. With every thrust like that he either moaned or winced.  
His belly was covered by his shirt completely now, but with the way it stuck to his damp skin it might have not even been there. Every roll was visible through it. His chest was round and even a little bit perky. He looked delicious. Like you could just take a bite out of him and he would taste like candied bacon. His dick lay limp and small between his legs.  
With the hand holding him up at his butt she could feel how the waves coming from the impact of him falling down onto her rippled through the fat of his cheeks. The other hand was now holding up his thigh and it felt equally soft and delicious.  
If she wasn't significantly taller than him she might have felt small like that. With her slender frame against his wide hips, his belly rubbing against hers with the thrusting, his thighs around her waist, feet locked behind her back. He was so much girthier and rounder than her, but the height difference still made her feel huge. And with her being so much taller all his girth just added to making him look soft and tiny. Especially with her defined arms lifting him up by his soft and squishy ass and thighs, with her toned belly rubbing against the rolls of fat that were jiggling with every movement.

Lifted up like that their faces were just about at the same height and she kept looking him in the eyes. The bright baby blue looked almost grey in the light of the moon.  
She changed her pattern of movement. Instead of letting him fall down onto her she now held him more steady and thrusted up on her own with enough force to push him into the fence and make his back rub against the mesh. He'd get some beautiful scratches and red streams from that.  
He moaned out loudly with every thrust, having his entire body shook like that, feeling the impact of every thrust in every bone, joint and organ. His fingers where clenching hard onto the wire, the tips almost turning white and his eyes were shut closed.

“You're so beautiful.” Spinelli moaned out. “The way you look when you're gutted by this big, fat cock.”  
He moaned in an extra register.  
She couldn't quite believe how much he seemed to love being talked to like that.  
“Come on, baby boy, do you have another orgasm in you?”  
He didn't answer, just kept moaning.  
“Like it or not, I'll pull one out of you. Gonna drain you so hard you'll never have to jack off again.”  
His dick jerked at hearing that. Still soft, but giving off signs of life.  
“Do you want me to make you cum?” she asked.  
“Uhhhhh.....”  
“I can't hear you.”  
“Uhhhh yes...” he managed to get out.  
“You gotta keep holding your legs around me tight, so you don't slip, can you do that for me?”  
He nodded.  
“Good boy.”  
She removed her hand from his thigh and moved it around to his dick, taking it between her thumb and pointer finger and started moving up and down.  
He winced and noticeably tensed up.  
“Aww... overstimulated, are you? All tired out?”  
His moaning kept on getting louder and his body repeatedly went rigid and then limp again. He was probably clenching around her from the stimulation to his dick with all the both pleasurable and painful consequences of that.

His voice was scratchy and hoarse, but he kept getting even more vocal as he neared his third orgasm.  
When it hit he completely seized up. His half hard dick twitched, nothing coming out anymore, and he clenched down so hard that Spinelli could feel his butt suck her in.  
Afterwards he went completely limp and the weight on Spinelli drastically increased.  
She put her hand in the small of his back to support him and pushed them close together. His belly completely pressed against hers felt so soft, almost like a very warm and sticky teddy. He slung his arms around her neck and rested his head on her shoulder as she carried him back to the table and laid him down. She let the dildo slip out of him with a wet, squelching sound and looked at the slightly gaping hole before she lowered down his legs.  
Then she laid down next to him, putting an arm under his head and a hand below his shirt.  
Minutes passed without either saying anything, both catching their breath. Spinelli's arms hurt from carrying TJ for so long. She could only imagine how he must have felt.

“Should have made you lick it clean before I took you to the fence.” Spinelli muttered and then chuckled.  
TJ looked at her.  
“That... might have been fun.”  
“I don't think it's too bad though...” She smiled at him.  
“Can we do this again soon?” he asked.  
“Sure,” she said.  
“Thanks for showing me this,” he said doing his best to sound casual, and not like someone who might die of exhaustion any second now. “I owe you one.”  
“Oh I had my fun too.” She grinned at him.  
“Everything hurts...”  
“It does that...”  
“I'd go for another round though if I could still feel my legs.”  
“You should worry about getting home first.”  
He laughed.  
“I don't think I can walk.... or that I should show up like this at home.”  
Spinelli sighed.  
“You can stay over at my place, get some sleep and take a shower tomorrow, but you ain't getting breakfast in bed.”  
“Uhm...” he looked away, embarrassed.  
“What?”  
“That thing about... I can't walk... that wasn't a joke. I think I'd fall.”  
She pinched the bridge of her nose.  
“Fiiine, I will carry you since it isn't far, but I ain't putting pants on you, you take the walk of shame butt ass naked and if people see they will see.”  
Really this wasn't actually such a bad idea. Most people in the neighborhood mind their own business well enough, but if someone saw him and saw what she did to him, that wouldn't actually be so bad.

She put her pants back on and then put both their discarded clothes as well as the dildo back in her backpack.   
“Ready?” she asked as she extended her hand, then took his and pulled him upright and took him in her arms, pulling him off the table.  
He was passed out in her arms before they even reached her home.

**Author's Note:**

> Hope you enjoyed it. I gladly welcome criticism in the comments.


End file.
